1,3-diphenoxy-4-(phenylthio)-3-buten-2-one | 181355-12-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,3-diphenoxy-4-(phenylthio)-3-buten-2-one
• 英文别名: (Z)-1,3-diphenoxy-4-phenylsulfanylbut-3-en-2-one
• CAS: 181355-12-4
• 化学式: C₂₂H₁₈O₃S
• 分子量: 362.449
• InChiKey: GAWDXYLZYXQKTH-XLNRJJMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-diphenoxy-4-(phenylthio)-3-buten-2-one 在 三乙胺 作用下， 以 乙醚 、 xylene 为溶剂， 反应 50.5h， 生成 (3aS,4S,7R,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-4,6-diphenoxy-2-phenyl-7-phenylsulfanyl-3a,4,7,7a-tetrahydro-isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis and Diels−Alder Reactions of 4-Substituted- 1,3-diphenoxy-2-[(tert-butyldimethylsilyl)oxy]-1,3-butadienes:  Application to the Synthesis of Triaryl Ethers

  摘要：

  A novel class of tetrahetero-substituted 1,3-dienes 1a-d having aryl ether substituents at the 1,3-positions were synthesized by enol silylation of 4-substituted 1,3-diphenoxy-3-buten-2-ones-3a-c. The 1Z,3Z configuration of 1b has been assigned by X-ray crystallography. The synthesis of triaryl ethers utilizing a Diels-Alder approach involved reaction of diene la with methyl acrylate to furnish a 3:1 mixture of endo- and exo-adducts. Conversion of the adducts to cyclohexenone 8 and aromatization with DDQ gave triaryl ether 9. Cycloaddition reactions of la, Ib with some conjugated alkenes exhibited excellent regiospecificity and endo stereoselectivity.

  DOI：

  10.1021/jo960105d
• 作为产物：
  描述：

  苯硫酚 、 4-(dimethylamino)-1,3-diphenoxy-3-buten-2-one 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 5.0h， 以78%的产率得到1,3-diphenoxy-4-(phenylthio)-3-buten-2-one
  参考文献：
  名称：

  Synthesis and Diels−Alder Reactions of 4-Substituted- 1,3-diphenoxy-2-[(tert-butyldimethylsilyl)oxy]-1,3-butadienes:  Application to the Synthesis of Triaryl Ethers

  摘要：

  A novel class of tetrahetero-substituted 1,3-dienes 1a-d having aryl ether substituents at the 1,3-positions were synthesized by enol silylation of 4-substituted 1,3-diphenoxy-3-buten-2-ones-3a-c. The 1Z,3Z configuration of 1b has been assigned by X-ray crystallography. The synthesis of triaryl ethers utilizing a Diels-Alder approach involved reaction of diene la with methyl acrylate to furnish a 3:1 mixture of endo- and exo-adducts. Conversion of the adducts to cyclohexenone 8 and aromatization with DDQ gave triaryl ether 9. Cycloaddition reactions of la, Ib with some conjugated alkenes exhibited excellent regiospecificity and endo stereoselectivity.

  DOI：

  10.1021/jo960105d